Photo by jan kelsey

Anna's Retreat holiday rentals

We found 3,544 holiday rentals — enter your dates for availability
Select from 14 houses, 10 flats and other holiday rentals to find the perfect place for your stay in Anna's Retreat. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as air conditioning and cable TV. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Anna's Retreat

Showing deals for:13 Nov - 20 Nov

Pathway to the airstream 😎
Incredible view of Caribbean Sea.
Exterior
Dinette table east view to St. John.
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
AU$1,253
for 7 nights, 1 home
AU$179 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Main level dining
Outdoor entertainment area
Property grounds
Patio off main level
Exceptional
(43 reviews)

Minutes from Magens Bay, gated property, large pool & outdoor entertainment area

St. Thomas

8% off
AU$5,994
for 7 nights, 1 home
AU$856 per night
includes taxes & fees
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Room
Areal view og Cowpet Bat West.
Relax reading a book on the bench with ocean splashing in the background.
Rainbow from terrace and the dock below at the St. Thomas Yacht Club.
Exceptional
(82 reviews)

BELLA VISTA Villa - Cowpet Bay West; Beach, Pool, Restaurants, Views, & Breezes

St. Thomas

8% off
AU$5,584
for 7 nights, 1 apartment
AU$798 per night
includes taxes & fees
BELLA VISTA Villa - Cowpet Bay West; Beach, Pool, Restaurants, Views, & Breezes
Ocean View from your deck
Down Island View!
Kitchen/Dining
Bathroom
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

8% off
AU$5,287
for 7 nights, 1 apartment
AU$755 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Lounge area
Property grounds
Property grounds
Cliff and ocean view from main bedroom 2
Exceptional
(23 reviews)

Villa Mangorosa

St. Thomas

8% off
AU$7,668
for 7 nights, 1 home
AU$1,095 per night
includes taxes & fees
Villa Mangorosa
Pool
Dining
Living area
Room
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
AU$2,405
for 7 nights, 1 apartment
AU$344 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Living area
Living area
Interior
Living area
Exceptional
(41 reviews)

Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool

St. Thomas

8% off
AU$18,344
for 7 nights, 1 villa
AU$2,621 per night
includes taxes & fees
Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
Living area
Property grounds
Living area
Interior
Exceptional
(5 reviews)

The Ampersand Sky Villa: Iconic, Artful Luxury

St. Thomas

13% off
AU$4,895
for 7 nights, 1 villa
AU$699 per night
includes taxes & fees
The Ampersand Sky Villa: Iconic, Artful Luxury
Dining
Property grounds
Interior
Pool
Exceptional
(9 reviews)

Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!

St. Thomas

8% off
AU$2,872
for 7 nights, 1 apartment
AU$410 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Private kitchen
Pool
Dining
Outdoor dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

8% off
AU$4,237
for 7 nights, 1 apartment
AU$605 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Dining
Property grounds
Living area
Room
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
AU$7,636
for 7 nights, 1 villa
AU$1,091 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
Gorgeous view from anywhere in the condo.
Pain Killers to cold beer, the beach bar is your go-to for island cocktails
Schedule a sail for the afternoon, take a snorkeling excursion around St John's
Enjoy the afternoon at the resort's two-tier cascading saltwater pool.
Exceptional
(10 reviews)

Carribean Sea Just Steps from Your Patio!!

St. Thomas

8% off
AU$4,015
for 7 nights, 1 apartment
AU$574 per night
includes taxes & fees
Carribean Sea Just Steps from Your Patio!!
Overlooking the ocean
From the balcony
Hummingbirds flock these flowers
Bedroom
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
AU$3,714
for 7 nights, 1 apartment
AU$531 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Room
Deck at night
Private kitchen
Dining table
Exceptional
(70 reviews)

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

St. Thomas

8% off
AU$6,822
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Entrance
Ahhh...
Abi Beach below-beach bar and restaurant
Pool side dining
Exceptional
(152 reviews)

Private Paradise! One level, panoramic views from every room!

St. Thomas

8% off
AU$9,398
for 7 nights, 1 villa
AU$1,343 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
Interior
Exterior
Exterior detail
Room
Exceptional
(19 reviews)

Modern Cozy Studio 🎨 Shopping 🛍Historical 10 minute drive to 🏖

St. Thomas

7% off
AU$1,887
for 7 nights, 1 apartment
AU$270 per night
includes taxes & fees
Modern Cozy Studio 🎨 Shopping 🛍Historical 10 minute drive to 🏖
Interior
Exterior
Property grounds
Living area
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
AU$17,645
for 7 nights, 1 villa
AU$2,521 per night
includes taxes & fees
Home with panoramic views with access to private beach!
Villa from the pond in kayak
Property grounds
Property grounds
Private kitchen
Exceptional
(18 reviews)

"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

St. John

9% off
AU$3,975
for 7 nights, 1 villa
AU$568 per night
includes taxes & fees
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
Room
Interior
Aerial view
Private kitchen
Excellent
(20 reviews)

Cozy stay, next to lookout and 10 minutes for Magens Bay Beach

St. Thomas

5% off
AU$1,938
for 7 nights, 1 villa
AU$277 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Terrace/patio
Living area
Exceptional
(12 reviews)

Luxe Loft ❤️ of Downtown AC WiFi 5 minute 🚶🏽‍♀️to beautiful waterfront 🚤

St. Thomas

8% off
AU$2,442
for 7 nights, 1 home
AU$349 per night
includes taxes & fees
Luxe Loft ❤️ of Downtown AC WiFi 5 minute 🚶🏽‍♀️to beautiful waterfront 🚤
Living area
The view looking out from living room
Private kitchen
First bedroom has a king sized bed, ac, flat screen tv, bathroom
Exceptional
(166 reviews)

Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants

St. Thomas

8% off
AU$3,899
for 7 nights, 1 villa
AU$557 per night
includes taxes & fees
Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants
The Beach Bar with live music and grill on the property
Pool
Socially distant beach bar food menu and pickup area
Socially distancing beach bar area for taking a drink or lunch to the beach
Exceptional
(65 reviews)

Beach, Bed and Beyond! WiFi included , New Tiled Shower!

St. Thomas

9% off
AU$3,866
for 7 nights, 1 apartment
AU$552 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
This IS the view from our patio! 37 steps to the water! It has been remodeled.
Another view of the pool area.
View of condo from front door entrance.
Resort. Our condo is right at the tip of the arrow.
Exceptional
(215 reviews)

Oceanfront Ground Floor Condo. 37 Steps to the Water

St. Thomas

8% off
AU$3,673
for 7 nights, 1 apartment
AU$525 per night
includes taxes & fees
Oceanfront Ground Floor Condo. 37 Steps to the Water
Beautiful Oceanside pool at Watergate Villas
The tranquil sound of the waves is ever present. You just can’t beat the view.
Master bedroom
Fully equipped kitchen with brand new fridge, microwave, and all cookware
Exceptional
(25 reviews)

FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !

St. Thomas

7% off
AU$2,474
for 7 nights, 1 apartment
AU$353 per night
includes taxes & fees
FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Anna's Retreat getaway

Learn about the unique charm of Anna's Retreat with a stay in a holiday home rental. This city has something for everyone. Sapphire Beach and Trunk Bay are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Anna's Retreat

Are you looking for top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that makes Anna's Retreat a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mahogany Run Golf Course (1.5 mi / 2.5 km)
  • The Self Centre (6.9 mi / 11.1 km)

Exploring the natural landscape of Anna's Retreat

Whether you're looking for adventure or just want to take in the scenery, Anna's Retreat is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Sapphire Beach (2.8 mi / 4.5 km)
  • Trunk Bay (8.1 mi / 13 km)
  • Virgin Islands National Park (9.6 mi / 15.4 km)
  • Coki Point Beach (1.7 mi / 2.8 km)
  • Wyndham Sugar Bay Beach (1.8 mi / 2.9 km)
  • Frenchman's Bay (2 mi / 3.2 km)

Transport options to and around Anna's Retreat

Fly into St. Thomas (SPB-St. Thomas Seaplane Base), the closest airport, located 3.2 mi (5.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into St. Thomas (STT-Cyril E. King), which is 5.3 mi (8.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Annas Retreat?
Houses are the most popular type of holiday home in Annas Retreat, according to our data. Even if you've got a different idea in mind, Stayz has holiday homes in all sizes and shapes. Browse our many options to find your ideal fit.
How much does it cost to rent a holiday home in Annas Retreat?
A number of things can determine how much you'll pay for a holiday home in Annas Retreat, such as the length of stay, season and type of property. Still, all our holiday homes have something in common — excellent value. Simply enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Annas Retreat?
When you travel and the style and size of the property will determine the cost of your beachside stay. Click on your Annas Retreat travel dates to see all your options on Stayz. Can't live without a hot tub? Use our filters to choose the amenities and features you need.
Are there pet-friendly holiday homes in Annas Retreat?
Yes. You'll have your pick of 27 holiday homes that allow pets in Annas Retreat on Stayz. Our furry kids need a break too, so simply use our search function for pet-friendly holiday homes to find a pad where your doggie can lap up the good times.
Can I rent a house with a pool in Annas Retreat?
Tick the "pool" box in our filter tool and take your pick of eight houses with private pools in Annas Retreat on Stayz. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday home boasts a swimming pool.
What are popular home amenities in Annas Retreat?
Some of the most popular home amenities people prefer in Annas Retreat are a barbecue grill, a chef and an ocean view. Whether you're taking a trip with pals, family or even pets, Stayz holiday homes include the best amenities for making epic memories with the people that matter most.
Are there large group holiday homes in Annas Retreat?
You'll find two holiday homes in Annas Retreat that can accommodate 10 or more guests. Whether you're organising a family holiday or an event like an anniversary, there's enough room to get your group together under one roof.
Are there holiday homes in Annas Retreat that welcome kids?
Annas Retreat has 27 family-friendly holiday homes to choose from. And finding a stay that welcomes little ones is a cinch with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll also enjoy access to perks and conveniences such as dining rooms, kitchens and pools.
What are the top attractions for families in Annas Retreat?
There are tons of cool things to see and do with the family in Annas Retreat, including:
  • Sapphire Beach
  • Trunk Bay
  • Coki Point Beach
Are there one-bedroom holiday homes in Annas Retreat?
You'll find 14 one-bedroom properties in Annas Retreat to pick from. A one-bedroom holiday home is a superb choice if it's just two of you or if you're travelling on your own. Add in more privacy, convenience and space than a standard hotel, and you're bound to have an unforgettable trip.
Can I find two-bedroom holiday homes in Annas Retreat?
Gather your loved ones and relax in total privacy and comfort in one of the seven two-bedroom holiday homes Annas Retreat has to offer.
Are there holiday homes with WiFi in Annas Retreat?
Annas Retreat has 16 holiday homes with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to posting pics on social media, these Stayz homes make it easy to get online.
How can I find holiday homes with air conditioning in Annas Retreat?
Annas Retreat has 24 holiday homes where you'll be able to relax and recharge in air-conditioned comfort. To book a stay on Stayz offering this perk, enter your dates of travel and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Annas Retreat?
You should check with the Annas Retreat holiday property you're considering on Stayz as age restrictions vary. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Annas Retreat for?
The amount of time you can rent an Annas Retreat holiday home for depends on the property. Simply put in your preferred travel dates to view options offering extended stays. They include everything you need to make your extended break more comfortable and enjoyable, like kitchens and backyards. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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